Strategy, options, and decisions continued

Chris Combe (he / him)
6 min readSep 4, 2022
Photo by Victoriano Izquierdo on Unsplash

In my previous article I left a few stones unturned, that deserve exploration.

Wardley Maps / Mapping by Simon Wardley

Wardley mapping is one of my favorite practices to use as an architect, turned agile Padawan. What problem does Wardley mapping try and solve, its visualization of value over an evolutionary axis to facilitate a discussion towards shared understanding. I’m sure many of you have heard ‘all models are wrong; some models are useful’. Wardley mapping supports the useful model discussions.

Simon is a gem of a human being and freely shares his work online under creative commons (also available in other formats). He’s given many talks on mapping as well as other topics and I can highly recommend the Wardley mapping community.

Why would you use Wardley mapping? I’ve personally found it useful for discussing options, decisions and strategy around products and their underlying components. As a former domain architect, one of the scenarios I found myself in frequently was people wanting to either build something from scratch or buy something they had previously used at a prior organization or from market analysis (the market analysis isn't the issue, it is how it is often used).

Here’s a simple example from Simon’s online book.

There’s a lot more to Wardley mapping, including purpose, landscape, climate, doctrine, and leadership (nicely aligned to the OODA loop). There’s a lot more to it. I highly recommend exploring the work further but to get you initially interested — I suggest starting with one of Simon’s many talks.

Simon Wardleys book

I also recommend Ben Mosier’s amazing resources Learn Wardley Mapping.

Real Options by Chris Matts and Olav Maassen

I had the pleasure of sitting next to Chris Matts for a couple of years when we worked at the same company, he mentored me in the ways of lean, agile and so much more.

What is Real Options? Real Options has its roots in Financial Option Theory which is scary for most people, the point I’m trying to make is that there’s serious rigour behind it. Real Options applies Financials Options to the Real world when it comes to making decisions.

You can read up on the details further on Chris’ blog (theITRiskManager).

Real Options says:

  • Options have value
  • Options expire
  • Never commit early unless you know why *

* The latter nicely links with Preston Smith’s ‘Make the commitment at the last responsible moment’.

There is a lot more to the practice than the above 3 items and there’s a nice write up on InfoQ I recommend reading for the ‘how’ around the decisioning process. I see it as being useful because the practice puts you into the mindset of not over committing to ideas, equally getting you to consider all possible options and whilst many people often ignore black swan events as being improbable. Thinking through what would happen if such an event occurs allows you to plan / consider what you’d do in those situations.

Why would you use Real Options? To consider the future possible but without over committing to any one option. This gives you the ability to be agile in your thinking and not be fixed to a solution and it also allows you to break down options into smaller steps that allows you to defer options whilst still delivering something of value.

Chris even produced a graphic novel which you can get for free!

Cynefin by Dave Snowden

Cynefin is a sense making framework for dealing with uncertainty in the world. Cynefin breaks the world into domains. Cynefin is a Welsh word that means ‘Place of Your Multiple Belongings’. Some of these domains have gone through renames over the years e.g. simple, obvious, clear.

The work by Dave and his company ‘The Cynefin Company’ (formerly Cognitive Edge) is now freely available on their wiki here: https://cynefin.io/

I’ve observed from experience that practices are situational, and Cynefin explains that. Not all practices make sense in every situation. I often listen out for people using the term ‘best practice’ to see how they are using it and often strike up a conversation about Cynefin as a result. This is often something I see where people are asking for checklists or templates when it comes to agile transformation work. People are uncomfortable, they don’t have the experience and don't know the practices, so they want to be given templates to follow as scaffolding.

Be careful with templates, they can serve a purpose if created thoughtfully but you should avoid spoon feeding people as that prevents them from thinking independently and learning from experimentation and observation.

Why would you use Cynefin? The more you learn about Cynefin, the more you realise it can be applied generally. Cynefin helps you situate yourself and gives you a framework for how to act in that context. This made sense to me, when I heard Dave point out that users don’t know what they want until they see it.

When building products, especially new ones that teams haven’t built before, the work sits in the Complex domain. The needs are not clear as you are often solving a new problem for the first time. Needs emerge and cannot be written down and in many cases we don’t even know how to build the new product. Instead, running multiple safe to fail probes gives you a way to find out what is most valuable to your users, so consider doing this early and often to find your value.

The practices you use in a Complex context are different and more exploratory and allow you to quickly run multiple probes in parallel to find out what works and what doesn’t.

Check out the video below on Rewilding Agile for more on that.

Source https://cynefin.io/wiki/Cynefin

Ordered

In Clear, you can apply a best practice to a situation (e.g. a checklist, knowledge base article) and there is one way of doing things. This is the type of context where everyone knows what to do and the approach is obvious.

In Complicated, you rely on the guidance of experts for Good practices to apply (e.g. a mechanic, accountant, doctor), the world is knowable but requires expertise.

Complex

In Complex, there are ‘Exaptive’ practices which is an evolutionary term to describe taking practices from other disciplines and applying them in a new way (e.g. the human body). The option here is to perform multiple ‘safe to fail probes’ (in parallel) to see what works best.

Chaotic

In Chaotic, there are no defined practices, and instead they tend to emerge from taking an action and sensing for input (e.g. when the COVID pandemic started and there was not known vaccine). This domain is typically a situation where a crisis starts out and people don’t know what works or is effective.

Confusion & Aporia

The Confused and Aporetic domain (the 5th) is represented by the state of confusion and being in potentially multiple states as once. This domain is often jokingly referred to by Chris Matts as the 5th quadrant, mostly meant as a poke at Dave. I’ve not explored this domain as much as the others, I would summarize as a state of confusion of puzzlement. Clearly this isn’t a place to stay long!

There’s more to the domains and other domains to explore, I wanted to keep things concise for readability. More on the Cynefin domains wiki

Check out one of Dave’s more recent talks on Cynefin.

Dave’s more recent take on ‘Rewilding Agile’ with his Complexity science lens is also quite interesting too.

Dave’s Cynefin language can be overwhelming the first few times you try and get your head around things. As such the following supporting articles might give you a softer landing.

What other decision and sense making frameworks have you found to be useful on your travels?

Beware, these topics will lead you down a rabbit hole but are worth the exploration. I’ve been learning about them for a couple of years already and continue to be surprised when I find a new opportunity to use these frameworks.

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Agile architect (socio-technical), coach, ways of working enthusiast. Professional nerd, recovering CTO, explorer, retired DJ and enthusiast of tasty food